Synthesis, optical, thermal, and redox properties of 2,3,9,10- tetrasubstituted- 6,13-dialkynylpentacenes

John E. Anthony; Christopher R. Swartz; Chad A. Landis; Sean R. Parkin

doi:10.1117/12.615939

Synthesis, optical, thermal, and redox properties of 2,3,9,10- tetrasubstituted- 6,13-dialkynylpentacenes

John E. Anthony
, Christopher R. Swartz
, Chad A. Landis
, Sean R. Parkin

Producción científica: Conference article › revisión exhaustiva

4 Citas (Scopus)

Resumen

A series of 2,3,9,10-tetrasubstituted-6,13-dialkynylpentacenes was synthesized and their properties evaluated. Various alkynes with different substituents were chosen to explore the effects of substitution on acene properties. The addition of alkyl groups to the pentacene 2,3,9,10-positions showed significant effects on the absorption, emission, and redox properties versus the non-alkylated (R = H) materials. The acenes exhibited excellent solubility in numerous solvents, and HOMO energy levels matched well with the work function of gold, an important electrode material. Crystallographic characterization of the methoxymethylene derivative showed it to adopt a 1 -dimensional π-stacked arrangement, with good overlap of the aromatic faces.

Idioma original	English
Número de artículo	594002
Páginas (desde-hasta)	1-12
Número de páginas	12
Publicación	Proceedings of SPIE - The International Society for Optical Engineering
Volumen	5940
DOI	https://doi.org/10.1117/12.615939
Estado	Published - 2005
Evento	Organic Field-Effect Transistors IV - San Diego, CA, United States Duración: jul 31 2005 → ago 2 2005

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Condensed Matter Physics
Computer Science Applications
Applied Mathematics
Electrical and Electronic Engineering

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title = "Synthesis, optical, thermal, and redox properties of 2,3,9,10- tetrasubstituted- 6,13-dialkynylpentacenes",

abstract = "A series of 2,3,9,10-tetrasubstituted-6,13-dialkynylpentacenes was synthesized and their properties evaluated. Various alkynes with different substituents were chosen to explore the effects of substitution on acene properties. The addition of alkyl groups to the pentacene 2,3,9,10-positions showed significant effects on the absorption, emission, and redox properties versus the non-alkylated (R = H) materials. The acenes exhibited excellent solubility in numerous solvents, and HOMO energy levels matched well with the work function of gold, an important electrode material. Crystallographic characterization of the methoxymethylene derivative showed it to adopt a 1 -dimensional π-stacked arrangement, with good overlap of the aromatic faces.",

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doi = "10.1117/12.615939",

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AU - Anthony, John E.

AU - Swartz, Christopher R.

AU - Landis, Chad A.

AU - Parkin, Sean R.

PY - 2005

Y1 - 2005

N2 - A series of 2,3,9,10-tetrasubstituted-6,13-dialkynylpentacenes was synthesized and their properties evaluated. Various alkynes with different substituents were chosen to explore the effects of substitution on acene properties. The addition of alkyl groups to the pentacene 2,3,9,10-positions showed significant effects on the absorption, emission, and redox properties versus the non-alkylated (R = H) materials. The acenes exhibited excellent solubility in numerous solvents, and HOMO energy levels matched well with the work function of gold, an important electrode material. Crystallographic characterization of the methoxymethylene derivative showed it to adopt a 1 -dimensional π-stacked arrangement, with good overlap of the aromatic faces.

AB - A series of 2,3,9,10-tetrasubstituted-6,13-dialkynylpentacenes was synthesized and their properties evaluated. Various alkynes with different substituents were chosen to explore the effects of substitution on acene properties. The addition of alkyl groups to the pentacene 2,3,9,10-positions showed significant effects on the absorption, emission, and redox properties versus the non-alkylated (R = H) materials. The acenes exhibited excellent solubility in numerous solvents, and HOMO energy levels matched well with the work function of gold, an important electrode material. Crystallographic characterization of the methoxymethylene derivative showed it to adopt a 1 -dimensional π-stacked arrangement, with good overlap of the aromatic faces.

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DO - 10.1117/12.615939

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SN - 0277-786X

VL - 5940

SP - 1

EP - 12

JO - Proceedings of SPIE - The International Society for Optical Engineering

JF - Proceedings of SPIE - The International Society for Optical Engineering

M1 - 594002

T2 - Organic Field-Effect Transistors IV

Y2 - 31 July 2005 through 2 August 2005

ER -

Synthesis, optical, thermal, and redox properties of 2,3,9,10- tetrasubstituted- 6,13-dialkynylpentacenes

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